通过Pd/NBE-催化1,2-功能化糖组装C-基糖化物
Penggang Zhao1, Qirui Yin1, Muhammad Nasir Siddique1
1Department State Key Laboratory of Applied Organic Chemistry, Department of Chemistry Institution, Lanzhou University, Lanzhou 730000, PR China.
The Journal of organic chemistry
|May 30, 2025
概括
合成C-基糖化物,对于天然产品和药品至关重要,是具有挑战性的. 这项研究引入了Catellani反应方法,用于从基化物中高效,区域选择性的C-基糖化物组合.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 在许多生物活性天然产品和制药剂中,C-基糖化物是重要的结构单元.
- 有效和区域选择性合成C-基糖化物仍然是有机化学的一个重大挑战.
研究的目的:
- 开发一种新的合成策略,用于直接和区域选择性组装C-基糖化物.
- 为了克服与传统C-基糖化物合成方法相关的局限性.
主要方法:
- 利用卡泰拉尼反应直接将基化物与甘氨基基 donor 结合起来.
- 探索了C-葡萄糖体结构中卡特拉尼反应的范围和局限性.
主要成果:
- 成功演示了一种支持卡泰拉尼反应的方法,用于从基化物中合成C-基糖化物.
- 在广泛的基板上实现了完美的区域控制和卓越的功能组耐受性.
- 确定了Catellani反应对这种特定合成转化的有效性.
结论:
- 开发的Catellani反应协议为C-基糖化物合成提供了一种高效和多功能方法.
- 这一进步显著扩大了Catellani反应在构建复杂的C-糖化物中的实用性.
- 为获取与药学相关的C-基糖化物化合物提供了一种有价值的工具.
相关概念视频
C–C Bond Formation: Aldol Condensation Overview
13.5K
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
13.5K
Oligosaccharide Assembly
2.8K
Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
Multiple sugar molecules that may or may...
Multiple sugar molecules that may or may...
2.8K
Base-Catalyzed Aldol Addition Reaction
3.3K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
3.3K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
3.4K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.4K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
5.9K
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
5.9K
Preparation of Diols and Pinacol Rearrangement
3.3K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.3K


